TITLE    : The New Hire
STORYID  : the-new-hire-1
SUMMARY  : Their jobs required more than driving or answering phones.
AUTHOR   : Cal Y. Pygia@lit
DATE     : 2008-10-27
CATEGORY : transgender-crossdressers
FLAGS    : 
TAGS     : |work|shemale|transsexual|anal|


Norman Bancroft wasn't exactly crazy about the job. For one thing, the pay sucked, and there was zero chance for promotions. In addition, fairly long periods of boredom were relieved--if one could call driving several hundred miles per day for several days in a row relief--by trips from one of the railroad's distant job sites to another somewhere in the northwestern quadrant of the United States. At least the job driving workers from site to site paid the bills. It offered a change of scenery, too, but the long hours behind the wheel and a sore back were stiff prices to pay to see the U. S. A.



The company didn't care much about its drivers, that was clear enough, but they took good care of the railroad workers. They were paid well, had great benefits, and Norm's interviewer had made it clear that he, if hired, was to do all that he could to satisfy his passengers. "It's very important to keep the men happy," he'd been told. Norm had assured him that he'd so anything he could to keep the men happy. How hard could that be? he'd asked himself. In his experience, rough-hewn men had pretty simple needs.



He'd been thankful when, a week later, he'd received the word that he'd been hired. He was welcomed "aboard" as an R &amp; R Drivers employee and assigned keys to a late-model passenger van. Today was his first time out.



So far, everything had gone predictably well. He'd loaded his passengers--he supposed he ought to say "boarded" them--and they'd already put fifty miles behind them, the guys talking mostly among themselves. As he drove the vehicle past towering pines, toward a stretch of mountains ahead of them, under a cloudless, azure sky, Norm heard snatches of their conversation. Predictably, it consisted mostly of jokes and double-entendres about sex. 



"The wife asks, 'The first time you ever saw me naked, what did you think?'" Ben, the pot-bellied man with the big hands who'd initiated the joke, answered for the woman's husband: "I wanted to fuck your brains out and suck your tits dry." After a pause, he continued, "As she removed the last of her clothing in preparation for her evening shower, she asked, 'What are you thinking now?' Looking her naked body up and down, he replied, 'It looks as though I did a pretty good job!'"



The other two men, Sam and Ed, guffawed.



"Damn, that's a good one, Ben!" Sam cried.



"Just don't let Bobbie hear anything like that," Ed warned.



Bobbie Lee was the next traveler on Norm's passenger list. He was to pick her up in Jasper, about a hundred miles north of their present location.



"Fuck her," Sam said.



"You'd like to, I have no doubt," Ed quipped.



"The bitch is most likely a lesbian, anyway," Ben opined. "What right-minded woman would want to work with you pricks?"



Sam and Ed laughed again.



"She's a secretary," Ed pointed out. "It ain't like she's going to get her dainty little hands dirty doing real work."



"Not on you, that's for sure," Ben agreed.



"Speaking of Bobbie inspired me," Sam said. He meant he had a joke of his own to tell.



Ed groaned, rolling his eyes.



"Let's hear it," Ben said.



So far, none of his passengers had included Norm in their repartee. It was just as well, Norm thought. He was content to listen.



"Okay, here it is," Sam announced: "A transsexual is being interviewed on a radio talk show. The host asks, 'When you became a woman, what sort of pain did you experience during the operation?' The transsexual replies, 'When they cut my penis off, it didn't hurt as much as I thought it would. And when they put the silicone implants in my chest, that didn't hurt too much, either.' Amazed, the host said, 'Wow! Then you didn't experience any pain at all?' The transsexual replied, 'I never said that. It hurt like hell when they removed half my brain and doubled the size of my mouth!'" Finishing his joke, Sam laughed heartily, but the others were silent.



"Come on," Sam said. "That joke was funny, and you know it!"



"It was lame," Ben said.



"It was hilarious," Sam cried.



"It was stupid," Ed maintained.



"You just don't have a sense of humor." Sam looked to Ben. "It was funny, wasn't it Ben? Tell this humorless numbskull my joke was funny."



"Let's leave it up to the driver," Ben suggested. He called to me from the back of the van. "So, what do you think, Norman? Is Sam's joke funny?"



Norm was surprised Ben knew his name. Norm had been ignored for the past two hours, but now, he was being included, all right--but not merely as a listener; they'd called upon him to settle their dispute. Sam thought his joke was hilarious, Ed thought it was lame, and Ben had been non-committal. Whichever way Norm answered, he'd probably end up offending somebody. He shrugged. He might as well answer honestly, he thought. "It wasn't half bad," he said.



"What kind of lame-ass answer is that?" Ed wanted to know. "Either Sam's joke was funny--which it wasn't--or not. Which was it?"



"Now, now, boys," Ben's bass voice boomed from the rear of the vehicle. "I think Norman's answer was perfect. Obviously, he didn't want to offend either one of you pantywaists, so he gave a middle-of-the-road response. Very diplomatic, Norman."



Norm chuckled. "Not all that diplomatic, it seems," he told Ben. "Two out of three of you are pissed off, anyway."



"That's because they're dickheads," Ben said.



"Ed is not a dickhead," Sam declared.



"Thanks, Sam," Ed said.



"He's a peckerwood," Sam clarified.



"See what I mean, Norman?" Ben said to the driver. "They're dickheads."



"Your answer wasn't half bad, Norman" Ed relented.



"No, it wasn't," Sam admitted. He paused. "Of course, that means it wasn't half good, either."



Norm shrugged. "I'll settle for that."



"Just don't repeat Ed's joke in front of Bobbie," Sam advised, "not if you know what's good for you."



"She's really a prude, huh?" Norm asked.



The three passengers guffawed, Sam slapping his knee.



Between wheezing gasps, tears running down his cheeks, Ben, managed to state, "Norman's funnier than either one of you, and he ain't even trying to be funny."



Norm had no idea why the men had thought his straightforward question humorous, but he didn't care. It was enough that they'd finally deigned to talk to him. "Do me a favor, guys," Norm called to his passengers.



"What's that?" Sam asked.



"Call me 'Norm.'"



"You got it, Norm," Ben wheezed, red-faced from chuckling.



The laughter started again, and Norm wondered what had been so humorous about his asking whether Bobbie was a prude.







Norm drove the van through steeper terrain. On either side of the interstate highway, the pines thickened, and their shadows darkened the roadway. The slight chill in the air became colder, and Sam asked that the heater be turned on. The other passengers objected to his request, so, once again, Norm was caught between their conflicting desires. He recalled the interviewer's insistence that he satisfy his passengers' every wish. The fucker hadn't told Norm that their wishes seldom ever seemed to mesh. Why couldn't the fuckers just kick back and enjoy the scenery? The tall, snowy peaks of the blue mountains were beautiful, as was the thick forest of evergreens. They were driving through some of the most beautiful countryside in the world, and all they could think of to do was to bitch about whether to turn on the van's heater.



"You going to turn the heater on or not?" Sam demanded.



"We don't need no fucking heater blasting our asses," Ed declared.



"We can live without it," Ben agreed.



"Why don't we let Bobbie decide?" Norm suggested. "I'll be picking her up in about ten minutes."



They considered Norm's proposal. He figured they'd reject it, without consideration, but the burly bastards surprised the driver by agreeing to the idea.



"Bobbie will want heat," Sam predicted. He wore a smug smile, as if her decision had already vindicated his request that the van's heater be activated.



"I'll give her all the heat she can stand," Ben returned, "and I don't need any fucking machine to help me provide it."



"In your dreams," Sam told him.



Norm rolled his eyes. If he didn't need this job so bad, he'd have pulled onto the shoulder and ordered his passengers to hit the road. He didn't need this shit.



Unfortunately, he did need the money.







By the looks of her, Norm thought, as he helped Bobbie with her luggage, she wouldn't need any help from the heater. She was hot!



Statuesque and willowy, with long, wavy black hair and dark eyes enhanced by thick, long lashes and expertly applied mascara, she had a slender, delicate nose; high cheekbones; full, sensuous lips; and a pointed chin. Her complexion was flawless and smooth, and her face had the shape of a Valentine's heart. She had high, full, round breasts--implants, maybe--a flat tummy; a narrow waist; long, tapering thighs and firm calves; and a gorgeous, full, round, firm-soft bottom that made Norm's cock hard. He watched the lovely moon sway and dip, tightening and relaxing as she climbed the steps at the side of the van and entered the vehicle to her fellow passengers' wolf whistles and crude compliments.



Norm was shocked to see that Sam had opened his fly and extracted his cock, which, like Norm's own prick, was rock hard. "Here, honey," Sam said to Bobbie, leering, "you can sit on this."



Norm thought of ordering Sam to zip both his lip and his fly, but he decided he'd let Bobbie handle him, if she could. He was supposed to satisfy his charges, not piss them off. Besides, it would be fun to see what Bobbie the Prude would do.



Norm didn't have long to wait to see. She shoved her hand down, hard, on the upright cock, grinding it under her palm as, pretending to lose her balance, she climbed past him and took the empty seat by the window. "Thanks, but no thanks, Sammy," she told him. "I prefer a seat with a view."



Ben and Ed laughed as their companion turned every shade of red between pink and scarlet.



Bobbie gave Sam's cock a contemptuous look. As she turned her gaze to the sylvan view outside her window, she remarked, "There's certainly nothing to look at there."



The others, Norm included, laughed again. Bobbie was beautiful, and she was hot, and, as she'd just proved, beyond all doubt, she most certainly wasn't a prude!







An hour later, Norm pulled the van into a motel parking lot. Dusk had settled into dark, and his passengers, like their driver, were road weary enough for one day. R &amp; R Drivers had pre-paid for their accommodations, such as they were--the company didn't spend much on employee comfort. The place seemed safe enough, and clean, if rather Spartan. Norm wasn't complaining. He wasn't finicky. A hot shower, a heater, a TV, preferably with a porn channel, and a serviceable bed was all he needed. He checked himself and the others into their rooms. He had Number 10, and Bobbie was in Number 11. Their rooms shared a connecting doorway, the desk clerk advised Norm. Ben, Sam, and Ed would bed down further along the row of apartments.



He helped them with their luggage before, entering his room, he removed his clothes and stepped under the hot darting needles of a steaming shower. The heat of the water felt wonderful, as did his ability to stand after sitting down all day, behind the wheel of a van full of complaining passengers. Only Bobbie had refrained from making demands and whining about this, that, or the other thing. 



As he showered, whirling the soapy washcloth over his firm, well-defined pectoral muscles, his firm, flat belly, the sopping black thatch of his pubic hair, and his burgeoning erection, Norman, eyes closed, remembered how sexy Bobbie had looked the first time he'd seen her in her red mini-skirt; matching knee-high, leather boots; and tight, green, crushed-velvet top, low cut enough to offer him a good sample of her marvelous cleavage beneath the blouse's tight-stretched fabric. She was a looker, all right. If he had her here, with him, now, Norm would--



His eyes opened, wide, and he strained to hear, turning off the shower. Water ran, tickling, down his chest, belly, back, ass, and thighs. Beads of water, standing upon his rippling muscles, jiggled, broke, and trickled down his glistening body. His cock, still erect, bobbed and wavered as he tensed, ready for action.



He thought he'd heard a door open.



The acoustics in these shoddy motel hells weren't all that great, and he wasn't sure, but the door had sounded as if it might be his own, which would mean that someone had opened it, entering his room. Since only the desk clerk or a maid was likely to have a passkey, it may have been one of them. If they'd knocked first, which protocol required, they'd knocked damned faintly, he thought. Norm was in great shape physically, from his eardrums to his testicles. He'd have heard a proper knock, even over the noise of the shower.



He eased open the shower door, leaving it ajar. Not bothering to wrap a towel around his waist, he stepped cautiously and quietly across the bathmat and the tiled floor.



He reached for the bathroom doorknob. Just as he was about to turn it, the door opened, and he saw Bobbie, as naked as he was, standing on the other side, a naughty smile on her lovely face.



Norm's eyes widened. "Bobbie! What the hell--"



She placed a forefinger against his lips. "I was lonely, Norm," she said, her voice soft and sultry. "I needed company."



He'd forgotten about the connecting door, which explained Bobbie's unannounced presence. "Don't think I'm not glad to have you," he said, "but you should have knocked. I thought I was being burglarized. I might have hurt you--unintentionally, of course."



She smiled. "Of course."



Her fingers trailed down his chest and his stomach, to close gently, about his risen scrotum, squeezing his balls lightly in her closing hand as her mouth, finding his, kissed him firmly, insistently, her lips parting as her moist tongue probed his mouth. 



Norm's cock stiffened further, his balls aching. His hands slid down her sculpted back, over her waist, and followed the swelling curves of her firm-soft, sleek buttocks.



"Do you want me, Norm?" she whispered, her voice husky in his ear.



"Yes," he declared.



She stepped closer to him, and Norm felt something odd press against his lower belly--something cylindrical and firm, yet yielding, and something else, too--with sudden recognition, Norm understood what Bobbie had pressed against him: a half-erect cock and a pair of balls!



She was a he--or a he-she, at any rate--a shemale!



Norm drew away, staring at the diminutive erection and the tiny balls inside the taut little pouch of her scrotum. He hadn't noticed her male genitalia during their brief exchange of dialogue after she'd opened the bathroom door. His eyes had been on her face, not her groin, and she'd stepped close to him so quickly that he hadn't had a chance to see her nudity beyond a glimpse of proud, womanly breasts, full, high, and round and capped with pink nipples as pretty as the buds of a rose.



"Do you still want me?" she asked him. Her gaze, saucy and confident a moment before, now seemed uncertain.



Norm's grin left her no doubt concerning the sincerity of his words: "Even more!"



Their arms around one another's waists, they crossed the room to the king-size bed. Norm hadn't had a chance to try it out yet, but it proved satisfactory. He frowned at the beautiful transsexual. "Aren't you going to join me?" he asked her.



She nodded. "Of course, just not in bed--not yet, at any rate."



"What did you have in mind?"



"Lie across the bed, with your feet on the floor and your thighs spread wide," she said. "I like to suck cock while I'm on my knees. The submissiveness implied by such a position is way more erotic."



Norm smiled. It was refreshing to have a cock sucker who was a thinker to boot. He assumed the position she'd described, and Bobbie knelt on the carpet, between his parted legs.



Bowing down before him, her silken breasts dangling against his inner thighs and calves, she parted her luscious lips and, her moist, pink tongue extending its welcome, she took his erect penis into the warm-soft-wetness of her mouth. Norm, supporting his upper body on his elbows, with his head lifted from the mattress so that he could observe Bobbie in action, watched her raven tresses flounce and bounce as, her head bobbing up and down in a slow, steady rhythm, she pumped the ring of her lips back and forth over the sleek, saliva-lubricated column of his erection, her unladylike slurping sounds an exciting accompaniment to her conduct. She was an expert cock sucker, and she relished worshiping a man's manhood. She paused occasionally to lick the shaft of his penis, as if she were enjoying an ice cream cone, rather than a thick, hard prick, or to kiss and nuzzle his balls inside his contracted, velvet-soft scrotum.



"Mmmmm!" she moaned around his cock as her lovely face plunged down, her lips a tight circle around his swollen shaft. This time, he felt her nose touch his belly; she'd taken the entire length of his prick into her mouth and esophagus, deep throating him as few women possessed the skills to do, even after Linda Lovelace had shown them how to accomplish this amazing feat. With her mouth stuffed full of his cock, Bobbie looked up at Norm, her eyes twinkling mischievously, and the sight of her wide, dark eyes, the mirrors of her soul, gazing intently into his own, while, just below them, her pretty lips were wrapped around his stiff, hard organ, was almost more than Norm could take. A flutter in his loins warned him that orgasm was imminent, and, not wanting to come so soon, he pleaded, "Stop! I'm not ready to shoot my load, not yet!"



She released him, a strand of saliva stretching between her lower lip and the purple crown of his ruddy cock a tie that bound them--for an instant, at least, before it broke--and she stood, showing her partner a cock as stiff and swollen as his own.



Norm nodded toward her erection. "Should I?"



She shook her head. "Later, maybe. This time around, I'd prefer you to finish in my ass."



She joined Norm on the bed, lying on her stomach, and he straddled her. Holding his cock in his fist, Norm lowered his hips, sliding his erection into the deep cleavage of her silken ass. He felt the stiff shaft slide past the sleek walls of her buttocks. His glans met the stout resistance of her small, tight anus. Resolutely, he pressed forward, and the tip of his penis, stretching her asshole, penetrated her bottom, jabbing its way past her sphincter. He fed another inch of his prick into her ass, and another, and another, until all eight inches of his thick, hard manhood crammed her rectum and he'd entered her to his balls. He paused, feeling her anus flutter frantically about his invading member, as if in a desperate, but vain, effort to dislodge the trespassing organ. The quivering ring of muscle felt wonderful, clamping and releasing his cock in rapid movements that excited him even more, causing his prick to thicken further as its rigidity increased. If nature had intended the fluttering of her anus to repel his cock, the ploy had failed, for, instead, the protesting sphincter had merely stiffened his prick--and Norm's resolve.



Rolling his hips atop her buttocks, he jiggled his cock inside her anus, reminding her that he was there. His effort was rewarded with a low, passionate groan form her, which left him in no doubt that she was enjoying being stuffed full with his thick, hard prick. Norm smiled. In that case, surely she'd enjoy the sensation of being refilled even more. He raised his hips, feeling the shaft of his penis slide back through her tight anal embrace. When nothing more than the glans remained inside her asshole, he thrust hard and fast, driving his member through her impaled anus again, as deep into her rectum as he could reach, and, squirming beneath him like a fish on a hook, she groaned, as much with discomfort, it seemed to Norm, as with pleasure.

<hr pg="2" />Immediately, he retreated, not to spare her any distress, but in preparation for the next assault, and he launched himself down, deep into her depths, plumbing her bowels with his rock-hard cock. His balls slapped the lower curves of her skewered bottom, and he pressed them more firmly still into her sleek flesh.



"Uhhh!" Bobbie grunted.



Norm grinned. He loved it when a woman put herself into her work. He reached under her, his hands pulling against her thighs.



She got the message, and raised herself onto her knees, resting the weight of her upper body upon her elbows.



As she assumed this new position, Norm also pushed up and back, as if he were recovering from a pushup, and, balancing upon his toes and fingertips, his ass high in the air, above hers, he launched his cock hard into her depths, filling her interior with his massive member as all eight inches slid into Bobbie's ass. He withdrew only a couple of inches, driving them immediately back through her anus, and repeated this action twenty times or more, in rapid succession, jabbing his cock back and forth inside her asshole.



Beneath him, she gasped as her body was rocked before his thrusts, her boobs jiggling, her muscles flexing, and her ass flattening and rebounding with his every thrust and retreat. "Uhhh!" she moaned. "Uhhh! Uhhh!"



Norm fucked her even harder, delivering long, full strokes again, as rapidly as he'd just jabbed the shorter strokes into her ravished behind. He was awash in sweat, and he felt his body tire all at once, as if all the energy had been summarily drained from his physique. Ass fucking a woman in this position was extremely demanding, even for a man in his shape. By force of will, he held onto the faint and fleeting reserves of his strength, unmercifully pounding Bobbie's ass, his cock moving through her impaled anus and inside her rectum with the force and fury of a jackhammer.



Finally, even his iron will was no match for his flagging strength, and, just as he was about to pull out of her, he felt the tsunami of ecstasy flood through him, and, lungs pumping and heart pounding, he released his own tidal wave of passion in surge after powerful surge of his thick, warm, white semen, filling her ass with his seed. He groaned mightily, collapsing onto his side, the sight of her gaping asshole, slick with his smeared semen the last sight he saw before his eyes closed.



A moment later, he'd opened them again, to see Bobbie kneeling before him, her own cute cock and tiny balls in his face. "My turn, stud," she said.



"Give me a minute," Norm protested. "You've drained my strength, along with my cum."



"You're still plenty strong enough to lick it," she said, bringing her boyish genitals even closer.



She's right, Norm thought. He opened his mouth, let his tongue slip through his parted lips, and touched its wet, pink tip to her petite penis. The small, soft cock swung like a bell clapper as he licked it. He moved his face forward, feeling her small, velvet-soft scrotum as her diminutive balls pressed against his chin, and took her member into his mouth. It felt warm and wonderful, this dainty stalk of womanly cock, and he nursed it as if he were sucking a breast. Between his lips, the little penis blossomed, stiffening, as it swelled to fullness. He worked his head back and forth, letting the small organ slide between the "O" of his lips. She pressed her groin even more closely to him, and he felt her flesh against his brow. Sucking her cock was much better than sucking the long, thick, hard manly pricks Norm had sucked in the past, and, he had no doubt that doing so would be far superior to sucking the erect penises of his other passengers, Ben, Sam, and Ed, who'd want theirs sucked, too, soon enough.



Whether as a result of her estrogen regimen, due to psychological reasons, or as an effect of both, Bobbie managed to last a long time, which was fine with Norm. Sucking her cock was almost like sucking a woman's clitoris, except it was also rather like sucking a man's prick; it was a cross, as it were, between the two, he thought, and Norm enjoyed the sense that, in sucking Bobbie's shemale cock, he seemed to be enjoying both a woman's clit and a man's prick at the same time--and in the same person. A shemale's ability to evoke such thoughts and sensations was a large part of her mystique and her appeal, he thought.



When, half an hour later, Bobbie managed to come, she didn't ejaculate as Norm had done--and as Ben and Sam and Ed were sure to do. Rather than shoot several thick volleys of semen, she simply let fly with a half-hearted attempt at a gusher, following with two or three additional oozing presentations of sperm. Norm licked up the salty ambrosia, and the driver and his shemale passenger shared a sperm-slick kiss.



As they lay together, side by side, still naked, Norm asked her how she'd come to work for the railroad as a secretary. "Someone as beautiful as you should be in motion pictures," he told her, meaning every word.



"A secretary?" she repeated. "Is that what the boys told you I am?"



Norm looked puzzled. "Aren't you?"



She chuckled. "Hardly! I'm a whore, Norm--a prostitute on call exclusively to railroad workers. The guy who hired me, Ed's brother, Marty, made it clear what my supposed secretarial duties would be, and, believe me, there's a lot of dick taking but little or no dictation. When he hired me, Marty told me 'It's very important to keep the men happy.'"



Norm frowned.



"What is it?" Bobbie asked.



"That's what the bastard told me--the exact words."



"When he told me that, I knew he wasn't talking about answering the phone or dispatching the mail." She looked at Norm. "You must have known, too. Are you gay, Norm?"



Norm paused, then shrugged. "Bisexual."



"I figured as much. Marty, being Ed's brother, knows Ed and his buddies, Sam and Ben, are gay, so he won't hire anyone whose background check shows he isn't either gay or bi, or, as in my case--transsexual."



"I have an ex-wife and four kids to support," Norm told her. "The child support's killing me, but I'm not one to abandon innocent kids I helped to bring into this world. That's why I hired on. How about you?"



A tear collected at the corner of Bobbie's eye. "We all have our reasons," she said.



"What's yours?"



The tear spilled, meandering slowly down her cheek; another collected behind it. "It's a sad story. You sure you want to hear it?"



"I care about you, Bobbie, not just as a piece of ass, but as a person."



She smiled a rueful smile. "You sure know how to sweet talk a girl," she said.



"So tell me."



"It's my mom. She's alone. Dad died a couple of years back, and Mom's health has declined drastically. She needs a kidney, and she doesn't have insurance."



"You're doing this to buy her a kidney?"



Her mouth turned down, and she sobbed, the tears coming full force now. She nodded.



Norm kissed away her tears, holding her. They sat together for a long time, and Norm didn't think, even once, about her lips around his cock or his prick plunging into her wide-stretched anus.



Afterward, they made love again, slowly and deliberately, with tenderness greater than their passion, and they both recovered the hard-edged, false-front cynicism that protected them from the contempt of others who considered them better than a bisexual driver or a transsexual whore, despite the fact that they wouldn't hesitate to abandon their own kids if they ever divorced and couldn't be bothered to lift a finger to help their dying mothers.



Bobbie kissed Norm. "The boys will want to try you on for size, soon enough," she said.



Norm didn't look as if he welcomed her warning.



Playfully, she advised him, "You may need a seat cushion for the next week or so, but, if so, there's no need to worry--or buy one of your own--I have a spare you can borrow."



He smiled. "I'd quit this job, but I need the money and, besides, there is the fringe benefit of sleeping with Bobbie Lee."



She chuckled. "That's the only fringe benefit this company pays."



"That's plenty," he said, "for me."



They kissed again, and then the fists began to pound the door.



Bobby rose, kissed Norm again, and hurried through the connecting door, which she closed behind her.



Norm rose, and, naked, walked across the room to answer the door. It's very important to keep the men happy, he thought, especially now that he'd met Bobbie.

